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Brave or Crazy? Quitting my job to start my own a pandemic...

Have you always wanted to own your own business?

Do you have that entrepreneurial spirit?

Well, if someone had asked me those questions a year ago I would have said no.

Actually if you ask me right now I think I’d still say no…

I hear you asking, “But, Karli, don’t you own your own business now? Aren’t you an entrepreneur??”

Yes, I do.

And yes, apparently I am.

About a year ago, in late 2019, I got the crazy idea that my next career move could possibly be a pivot into the professional speaking and coaching world. A departure from Higher Education and Student Affairs where I have spent nearly a decade of my professional life. It was a wild idea, but hey, let’s go with it!

So I set out to start my own LLC - Karli Sherman Productions - and by the start of 2020 I was officially a business owner!

Which is bonkers because I literally knew nothing about starting, owning, or running a business.

I had to google what LLC stood for.

Y'all, seriously, I knew nothing.

The plan (was there a plan?) was to continue in my full-time job at the university where I was employed while I built my business up.

But rapidly the plan changed (again we are using “plan” loosely) and I decided to GO FOR IT.

Take the plunge,

Take the leap of faith,

Put all the eggs in a basket,

Charge forth,

whatever other optimistic cliche fits,

And I quit my job!

It was exciting! It was an adventure! It was March 2nd!

And then the world shut down two weeks later…

Yep, my last day at the university was March 2, 2020.

So I suddenly have a fledgling business based on speaking at events (which are all cancelled), educating teams (who are not meeting), and providing professional development for companies (who are not going into work) and campuses (who are shut down).


What a time to be a small business owner.

People have asked me constantly over the last 7 months, “Hey, how’s the new business going?!”

It’s a super nice question. I appreciate it.

I also struggle with how to respond.

Because I know what they are really doing is being encouraging and polite by recognizing my business.

So I should be positive and polite in my response, something like, “Oh it’s great, having tons of fun!”

But that response feels wrong.

Because, at best, it’s a half-lie.

And, at worst, it cheapens one of the most salient experiences of my life thus far.

But I can’t just dive into the professional, emotional, and financial intricacies of quitting a job and starting a business in a global pandemic. That doesn’t quite fit the social norm of appropriate responses here.

So what do I say?

My response changes each time, but it’s usually some combination of sentiments that express how harrowing it’s been while also being one of the best things I’ve ever done for myself.

I try to balance the polite positivity with some honesty and a dash of humor.

It usually works.

But what I really want to explain is...

The last year of my life has professionally challenged me in ways I haven’t experienced in years. Which is thrilling. And terrifying.

I’ve pushed myself so far outside my comfort zone I can’t even find that zone anymore.

I’ve learned so much about business and insurance and budgets and spreadsheets (there are so many spreadsheets why are there so many spreadsheets).

I’ve experienced Imposter Syndrome for the first time.

I’ve battled depression so deep I couldn’t see a way out.

I’ve met some of the most interesting, talented, dedicated, and fierce people in my community.

I’ve spent incredible amounts of money and made next to none.

I’ve found out people thought my business was my side hustle because they didn’t realize I left the university.

I’ve won awards, mentored people, gained certifications, and educated teams.

I’ve started to build my own dream for my life.

I’m 9 months in and I still am not entirely sure if this decision was brave or crazy.

I’m proud of myself.

I have a lot of support from family, friends, and colleagues.

I’m making a lot of moves that I know will set me up for long term success.

I’m lucky and I’m blessed.

And I’m scared.

People ask me if I regret quitting my university job.

Absolutely, unequivocally - no.

Actually, I only wish I had done it sooner so I would have established my business before this dumpster fire we call 2020 started.

Then why didn’t I start the business sooner?

Because I’ve never actually wanted to own my own business.

Which is kind of crazy, because now I wouldn’t have it any other way.

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About Karli

As the owner of Karli Sherman Productions, I am a professional speaker, leadership coach, and executive coach. I help companies, campuses, and individuals to level up and grow through professional development workshops, intensive coaching, and keynote presentations.

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